Both men are legends in the world of crime, and though we're all required to pick a favorite, this will no doubt be a lose-lose situation no matter who comes out the victor. Still, the conversation between these two guys would be worth the price of admission alone, if not for the fact that you'd also be guaranteed some serious hand cannon action. Who knows? Maybe when all is said and done, they can trade tips on how to please a woman.

Jules Winnfield

Samuel L. Jackson, "Pulp Fiction"
We will concede that there have been hundreds of men before Jules Winnfield who have quoted Scripture just before killing a man. How many, however, have eaten another man’s hamburger, drunk his Sprite, called his partner A Flock of Seagulls, and then recited Ezekiel 25:17 while emptying an entire clip into the dead duck-to-be? The one and only answer is our man in Englewood, the hit man of choice for resident crime lord Marcellus Wallace. If you need further proof of Jules’ badassity, all we have to say is: have you seen the man’s wallet?

Definitive badass moment: His systematic dismantling of Brett, the man with the suitcase. “‘What’ ain’t no country I ever heard of! They speak English in What?” Brett never had a prayer.

Classic badass line: “Oh, you ready to blow? Well, I’m a mushroom cloud- laying motherfucker, motherfucker! Every time my fingers touch brain, I’m Superfly TNT, I’m the Guns of the Navarone! In fact, what the fuck am I doing in the back? You’re the motherfucker who should be on brain detail!”

Seed: #5Occupation: HitmanStrengths: Unflappable, has God on his sideWeaknesses: Constantly in situations where someone is putting a gun in his faceBracket History: Defeated #12 Keyser Soze in round 2, 68%-32%

ALSO: Have something you want to say about this matchup or anyone else in our Badass Bracket? Blog about it at Premium Hollywood.

Tony Montana

Al Pacino, "Scarface"
What do you say about the most profane gangster in the history of profane gangsters? Local drug lord Frank Lopez secured a green card for a young punk named Tony Montana in exchange for killing one of his fellow Cuban refugees, and the Miami cocaine trade would never be the same. Tony’s rise to prominence was swift, thanks to his strict adherence to the tenets of success (“…when you get the money, then you get the power. Then when you get the power, then you get the women”), and there is no one in his crew that is too good to kill, which keeps his people honest. Sure, not everyone appreciates his brash style of management, but when the chips are down, Tony can always rely on his “little friend,” a combination M16 and grenade launcher.

Definitive badass moment: When Tony watches emotionlessly while his associate Angel is dismembered with a chainsaw during a drug deal gone wrong.

Classic badass line: “I kill a communist for fun, but for a green card, I gonna carve him up real nice.”